For me, Shogun MP, of course. It was a rare 4v4 that didn't lag, a lightly foggy battle on the Horselands map, with talented players on both sides, and two of my 47Ronin buddies teaming with me. I managed over 1500 kills, the most I ever got in a MP game, as we repulsed a very nasty attack which caught us off guard in the fog, and turned it around. I think I had less than 200 men left at the end. It was an extremely exciting game; at several points it seemed one side would win, but then someone would do something epic and the tide would turn. Ah, the glory days.
Runner-up was a neighborhood competition among friends, playing the original Soul Calibur on the Sega Dreamcast. There were 16 of us, all caught up in the SC thing that was the craze when it first came out. Most of them hadn't seen me play, but I'd seen most of them play (I'd hang out after work and watch; but often declined to play because I was so tired; I observed closely though ...). Using Mitsurugi, Taki, Siegfried, and Cervantes, I blasted my way into the final match. Then I played my hidden ace, and won the competition with my favorite freak. "VOOOOOLDO WINS!!," heh. It was quite a fun weekend.
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The most shameful moment was in 6th grade. I had a ~200 wins, 20 losses record on the chess team. Ten of those twenty losses were to one other player, our second ranker. Our school arranged a tournament with a nearby elementary school. I was defeated soundly in two games back to back and eliminated early in the match by an extraordinary player from the other school, their number one. It was so embarrassing. He just stomped me. I didn't play much chess after that.
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